4180-23-8 Usage
Description
Trans-Anethole, also known as (E)-Anethol, is a phenylpropanoid that is a naturally occurring flavoring agent. It is an alkoxypropenylbenzene derivative and an important favoring component of essential oils of more than 20 plant species. Trans-Anethole has insecticidal, larvicidal, and antimicrobial properties. It is a clear colorless to pale yellow liquid with a characteristic anise, sweet, spicy, warm odor and corresponding sweet taste.
Uses
Used in Flavoring Industry:
Trans-Anethole is used as a flavoring agent in the food and dentifrice industries due to its sweet, anise, licorice, and spicy taste with a lingering, sweet aftertaste.
Used in Perfumery:
Trans-Anethole is used in perfumery for soap and other products, as well as in some perfumes such as fennel, absinthe, and Hyacinth jacinthe.
Used in Pharmaceutical Industry:
Trans-Anethole is used as a flavor in the pharmaceutical industry and is also used in the culture media of Pseudomonas putida strain as a carbon and energy supplement.
Used in Photography and Microscopy:
Trans-Anethole is used in photography and as an embedding material in microscopy.
Used in Detergents:
Trans-Anethole is used in the production of detergents and has natural occurrence in star anise.
Used as a Platelet Aggregation Inhibitor:
Trans-Anethole is used to inhibit platelet aggregation, which can help prevent blood clots and related health issues.
Used in Anticancer Applications:
Trans-Anethole is used to inhibit lung and forestomach carcinogenesis, potentially offering therapeutic benefits in cancer treatment.
Used in Antifungal and Antioxidant Applications:
Trans-Anethole has been found to have antifungal and antioxidant activity, making it a useful compound in various applications.
Natural Occurrence:
Trans-Anethole is found in essential oils from seeds of anise (Pimpinella anisum L.), star anise (Illicium verum Hook.f), and sweet fennel (Foeniculum vulgare Mill. var. dulce). It is also found in fennel, aniseed, coriander, and many other volatile oils.
Preparation
By esterification of p-cresol with methyl alcohol and with subsequent condensation with α-cetaldehyde (Perknis); the
most common method of preparation is from pine oil. By fractional distillation of the essential oils of anise, star anise, and fennel;
the anise essences contain an average of 85% anethole; fennel, from 60 to 70%.
Preparation
By isomerization of estragole using alcoholic potassium hydroxide as agent (Arctander, 1969).
Synthesis Reference(s)
The Journal of Organic Chemistry, 50, p. 1797, 1985 DOI: 10.1021/jo00211a002Tetrahedron, 24, p. 2183, 1968 DOI: 10.1016/0040-4020(68)88120-7
Biochem/physiol Actions
Naturally occurring phenylpropene derivative that is estrogenic at lower concentrations and cytotoxic at higher concentrations to cancer cell lines. The cytotoxicity is related to the metabolism of trans-anethole to 4-hydroxy-1-propenylbenzene.
Anticancer Research
It is one of the major constituents of essential oil of fennel and anise and belongs tothe class of phenylpropenes. It has the capacity to block both inflammation andcarcinogenesis. It is an antioxidant and also a suppressor of NF-κB activation byIκBα degradation (Aggarwal and Shishodia 2004).
Metabolism
Anethole is metabolized by oxidation of the propenyl group and is excreted as anisic acid (Williams, 1959). The metabolism of trans-anethole used in the preparation of anis-flavoured alcoholic beverages was studied in the rabbit and rat after iv and oral administration. It was excreted rapidly from the animal regardless of the method of administration. After iv injection it was found concentrated in the liver, lungs and brain; after oral administration, absorption was slight and most of it remained in the stomach. Ethyl alcohol has no effect on the metabolism (Le Bourhis, 1968).
Check Digit Verification of cas no
The CAS Registry Mumber 4180-23-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,1,8 and 0 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4180-23:
(6*4)+(5*1)+(4*8)+(3*0)+(2*2)+(1*3)=68
68 % 10 = 8
So 4180-23-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
4180-23-8Relevant articles and documents
METHODS OF BORYLATION AND USES THEREOF
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Page/Page column 61-62, (2021/04/30)
The present invention relates, in general terms, to methods of borylation and uses thereof. In particular, the present invention provides a method of borylating an alkene compound by contacting the compound with a boron compound, a Fe pre-catalyst and a protic additive. The borylation occurs at a vicinal (β) position to an electron donating or electron withdrawing moiety of the compound.
Highly Z-Selective Double Bond Transposition in Simple Alkenes and Allylarenes through a Spin-Accelerated Allyl Mechanism
Kim, Daniel,Pillon, Guy,Diprimio, Daniel J.,Holland, Patrick L.
supporting information, p. 3070 - 3074 (2021/03/08)
Double-bond transposition in alkenes (isomerization) offers opportunities for the synthesis of bioactive molecules, but requires high selectivity to avoid mixtures of products. Generation of Z-alkenes, which are present in many natural products and pharmaceuticals, is particularly challenging because it is usually less thermodynamically favorable than generation of the E isomers. We report a β-dialdiminate-supported, high-spin cobalt(I) complex that can convert terminal alkenes, including previously recalcitrant allylbenzenes, to Z-2-alkenes with unprecedentedly high regioselectivity and stereoselectivity. Deuterium labeling studies indicate that the catalyst operates through a π-allyl mechanism, which is different from the alkyl mechanism that is followed by other Z-selective catalysts. Computations indicate that the triplet cobalt(I) alkene complex undergoes a spin state change from the resting-state triplet to a singlet in the lowest-energy C-H activation transition state, which leads to the Z product. This suggests that this change in spin state enables the catalyst to differentiate the stereodefining barriers in this system, and more generally that spin-state changes may offer a route toward novel stereocontrol methods for first-row transition metals.
Synthesis, antiepileptic effects, and structure-activity relationships of α-asarone derivatives: In vitro and in vivo neuroprotective effect of selected derivatives
Zhang, Jian,Mu, Keman,Yang, Peng,Feng, Xinqian,Zhang, Di,Fan, Xiangyu,Wang, Qiantao,Mao, Shengjun
, (2021/08/03)
In the present study, we compared the antiepileptic effects of α-asarone derivatives to explore their structure-activity relationships using the PTZ-induced seizure model. Our research revealed that electron-donating methoxy groups in the 3,4,5-position on phenyl ring increased antiepileptic potency but the placement of other groups at different positions decreased activity. Besides, in allyl moiety, the optimal activity was reached with either an allyl or a 1-butenyl group in conjugation with the benzene ring. The compounds 5 and 19 exerted better neuroprotective effects against epilepsy in vitro (cell) and in vivo (mouse) models. This study provides valuable data for further exploration and application of these compounds as potential anti-seizure medicines.